The C2 Selective Nucleophilic Substitution Reactions of 2,3-Epoxy Alcohols Mediated by Trialkyl Borates: The First endo-Mode Epoxide-Opening Reaction through an Intramolecular Metal Chelate

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Abstract
Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN3−(CH3O)3B, NaSPh−(CH3O)3B, or NaCN−(C2H5O)3B system. The reaction proceeds through novel endo-mode epoxide opening of an intramolecular boron chelate, which was suggested from both experimental and quantum mechanic studies.